Windsong villa close to Round hill
Listing Description
Windsong is an exquisite and very private home just four minutes from Round Hill. You will have spectacular views day and night and the most favorable tradewinds.
- 4-Bedroom deluxe private villa on 3 acres ~ spectacular ocean views east and west
- Open-air villa
- 20’ x 40’ Private tiled pool and poolside bar
- A full-time complimentary driver is included in full house rentals (4 bedrooms). Guests are responsible for all petrol.
- Full staff: butler, chef, housekeeper, gardeners, laundress
- Brand new 55“ UHD Samsung 6 Series TV ~ library of movie DVDs and music CDs
- High-speed DSL Internet access
- All bedrooms have air-conditioning, fans, safes, robes, and bathroom amenities
- Complimentary crib & highchair
- Glorious trade winds, breathtaking sunrises, and sunsets
- Tryall resort Membership
Villa is a beautifully designed and very private home conveniently located just minutes from Montego Bay’s renowned Round Hill property where guests enjoy complimentary beach membership.
This charming tropical villa encapsulates a complete Jamaican experience. Noted for its sweeping panoramic views, airy rooms, lush rolling landscape, and well-laid-out tropical gardens, is simply gorgeous and exquisitely inviting – from the outside in. The home and its elegant features cleverly blend the beauty of nature into the indoor settings and guests get an instant sense of serenity upon arrival.
The villa experience begins as soon as you turn onto the circular driveway encompassing the shade of our majestic banyan tree – resplendent with hanging orchids – and continues as you enter the welcoming courtyard with its vibrant tropical plants and water fountains inviting you to enjoy the finest of Caribbean living.
Unique hill located on the outskirts of Montego Bay is perfect to marvel at the most amazing views whilst enjoying the favorable trade winds of the season. The east view captures the rising sun over Montego Bay, while to the west is an equally lovely vista of Round Hill and breathtaking tropical sunsets above the lush green hills of Hanover. With soothing water features throughout, you will feel instantly welcome and at home. The well-cared grounds are thoughtfully filled with a variety of local tropical trees, plants and flowers, and fruit trees – the produce of which make it to the breakfast table when in season. Wander at leisure through this extensive garden and get to know Jamaica’s flora.
The villa is managed by a highly experienced team of staff who will ensure that your stay here meets and exceeds your expectations. The team will be happy to offer suggestions and recommendations when asked. Plan your meals with the skillful creative chef who will work with your tastes and dietary needs – serving up meal after sumptuous meal made from the freshest of ingredients, for your culinary delight. You may wish dinner to be served by candlelight indoors or in the more casual al fresco dining area on the verandah overlooking the pool. The poolside bar is kept stocked with ice and drinks for your convenience, and the sound system supplies music both indoors and out.
Accommodations
All bedrooms are 225 square feet in size and have state-of-the-art remote control quiet air conditioners.
Main Level
Master Bedroom
Queen-size bed; en-suite bathroom, double basin vanity, bathtub, and separate shower. DSL Internet access, Bose Wave Radio/CD. Two private balconies. Magnificent ocean views day and night.
Bedroom 2
King size or twin beds at guests’ option; en-suite bathroom with tub-shower combination. Sony radio/cassette/CD player. Private balcony. Magnificent view.
Lower Level
Bedroom 3
King size or twin beds at guests’ option; ensuite bathroom with tub-shower Combination. Radio/cassette/CD player. French doors to a private terrace and ocean view.
Bedroom 4
King size or twin beds at guests’ option; ensuite bathroom with tub-shower combination. Radio/cassette player. Television for watching DVDs and videos – no cable service in the bedroom. French doors to a private terrace and ocean view. While designed for children, this room is also perfectly suitable for adults.
Tryall Membership – A special amenity available to guests in this villa is membership at Tryall , just minutes from the villa and one of the finest private resorts on Jamaica’s North Coast. Tryall offers a beach, pool, chaise lounges, towels, jogging trail, gift shop, logo shop, library with computer, bar, afternoon tea, Wednesday Manager’s Cocktail Party, tennis courts, and unforgettable long sunsets from the waterfront terrace. For additional charges, members may enjoy the spa, Kids Club, fitness center, salon, a range of water sports, and beach parties.
There may be occasions when some or all the facilities of the hotel may be closed for membership guest services due to a private hotel event. Tryall reserves the right to change or alter its membership packages with no notice.
Rooms are for priced for double occupancy only. Some villas may allow extra guests, which must be approved by the homeowner and an extra guest fee may be applied. Check with your Villa Specialist. Rates are dynamic and subject to change without notice. Please confirm rate with your Villa Specialist at time of booking.
- Complimentary driver & 10-seat van on 7-night reservations (gas & gratuities are additional costs).
| Travel Dates | Bedrooms | Minimum Night Stay | Nightly Rates |
|---|---|---|---|
| High Season: 7-night minimum stay required Low Season: 5-night minimum stay required Holiday Season: 7-night minimum stay required (Easter Sunday, Thanksgiving, Christmas, and New Year’s Eve.) *Rates are subject to change without notice. Please check with your villa specialist to confirm. |
|||
| January 03, 2026 – April 03, 2026 High Season |
2 | 7 | $ 950 * |
| January 03, 2026 – April 03, 2026 High Season |
3 | 7 | $ 1430 * |
| January 03, 2026 – April 03, 2026 High Season |
4 | 7 | $ 1903 * |
| April 04, 2026 – April 11, 2026 Easter – Any 7 nights that includes Easter Sunday |
4 | 7 | $ 1903 * |
| April 12, 2026 – April 15, 2026 High Season |
2 | 7 | $ 950 * |
| April 12, 2026 – April 15, 2026 High Season |
3 | 7 | $ 1430 * |
| April 12, 2026 – April 15, 2026 High Season |
4 | 7 | $ 1903 * |
| April 16, 2026 – November 20, 2026 Low Season |
2 | 5 | $ 793 * |
| April 16, 2026 – November 20, 2026 Low Season |
3 | 5 | $ 1067 * |
| April 16, 2026 – November 20, 2026 Low Season |
4 | 5 | $ 1261 * |
| November 21, 2026 – November 28, 2026 Thanksgiving Holiday |
4 | 7 | $ 1903 * |
| November 29, 2026 – December 14, 2026 Low Season |
2 | 5 | $ 793 * |
| November 29, 2026 – December 14, 2026 Low Season |
3 | 5 | $ 1067 * |
| November 29, 2026 – December 14, 2026 Low Season |
4 | 5 | $ 1261 * |
| December 15, 2026 – December 18, 2026 High Season |
2 | 7 | $ 950 * |
| December 15, 2026 – December 18, 2026 High Season |
3 | 7 | $ 1430 * |
| December 15, 2026 – December 18, 2026 High Season |
4 | 7 | $ 1903 * |
| December 19, 2026 – December 26, 2026 Christmas – Dec 19-26 or 20-27 or any 7 nights that includes Dec 25th. Additionally, any 7 nights (eg, Dec 17-24) that prevent a Christmas reservation will be invoiced at the Christmas rate. |
4 | 7 | $ 2222 * |
| December 27, 2026 – January 02, 2027 New Year’s – Dec 26-Jan 2 or Dec 27-Jan 3 or any 7 nights that include Dec 31st. |
|||
Low Season: 5-night minimum stay required
Holiday Season: 7-night minimum stay required (Easter Sunday, Thanksgiving, Christmas, and New Year’s )
*Rates are subject to change without notice. Please check with your villa specialist to confirm.
Availability
| M | T | W | T | F | S | S |
|---|---|---|---|---|---|---|
| 1 | ||||||
| 2 | 3 | 4 | 5 | 6 | 7 | 8 |
| 9 | 10 | 11 | 12 | 13 | 14 | 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | 29 |
| 30 | 31 | |||||
| M | T | W | T | F | S | S |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | ||
| 6 | 7 | 8 | 9 | 10 | 11 | 12 |
| 13 | 14 | 15 | 16 | 17 | 18 | 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | 26 |
| 27 | 28 | 29 | 30 | |||





